At RetributionVantage won the Retribution Rumble and thus guaranteed himself a slot in the main event at Legacy against Chris McKenzie whom had successfully retained his championship against Gabriel Asar earlier in the night and guaranteed his own spot in the main event. It was announced by Mrs. Vanderbilt that a tournament would begin to crown new WEW Tag Team Champions after she forced Divas of Harlem to vacate the championships after they had failed to defend them within the last thirty days. The tournament finals are scheduled to take place at Legacy to crown the new champions which will be between Divas of Harlem, Men of War, The Natural Born Killaz and Venom. The annual Legacy Case Cash In match is also scheduled to take place with three Elitists: Kevin Kilbourne and WEW newcomers, Victor Mills & MinimiMax and three Starlets: Amber Torres, Rose Marino and newcomer C.J. Sweet participating.

One of the headlining matches going into the PPV is the one between WEW World Champion Shady Layne and B.O.S.S. (Ashley Tierney & Stasi Savage). On the May 19, 2014 Super Animosity, Tierney and Savage gloated about assaulting Shady Layne stated that they were going to end her reign as the leader of Adrenaline not her World Championship reign. This led to Shady coming out and challenging both members to a Handicap match at Legacy: Jamaica to which they accepted. This marks the first time that the WEW World Championship hasn't been defended at the Legacy PPV.

It was revealed that same night that the match between McKenzie and Vantage would be a Casket match after Vantage defeated Jake Gargano and earned the right to name the stipulation for the match. Also Mrs. Vanderbilt was challenged by Zharya Burke to a match for Control of WEW to which Vanderbilt agreed to before adding a No Disqualifications stipulation to the match.